Oxibendazole

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Oxibendazole
Oxibendazole.svg
Clinical data
AHFS/Drugs.com International Drug Names
ATCvet code
Legal status
Legal status
  • Veterinary use only
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ECHA InfoCard 100.039.873
Chemical and physical data
Formula C12H15N3O3
Molar mass 249.26 g mol −1
3D model (Jmol)
 NYesY (what is this?)  (verify)

Oxibendazole is a benzimidazole drug that is used to protect against roundworms, strongyles, threadworms, pinworms and lungworm infestations in horses and some domestic pets. It is usually white to yellowish in appearance, and may take the form of a powder or a tablet.

Synthesis[edit]

Oxibendazole synthesis:[1]

4‑Hydroxyacetamide (1) is alkylated with n-propyl bromide in the presence of potassium hydroxide to give the ether (2). Nitration of this product with nitric and sulfuric acids proceeds at the position ortho to the amide group (3), which is then reduced with SnCl2 to yield the phenylenediamine derivative (4). Reaction of that intermediate with S-methyl isothiourea proceeds first by aromatic cyclisation to the guanidine derivative followed by elimination of methyl mercaptan to yield the 2-aminobenzimidazole system (5). Acylation with methyl chloroformate results in the formation of a urethane on the amino group to produce oxibendazole (6).

References[edit]

  1. ^ GB 1123317  corresp to P. P. Actor, J. F. Pagano, U.S. Patent 3,574,845 (1968, 1971 both to Smith, Kline & French).